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Synlett 2022; 33(03): 273-276
DOI: 10.1055/a-1707-6593
DOI: 10.1055/a-1707-6593
letter
Concise Synthesis of the Terpene Core Structure of Suaveolindole through a Time-Economic Route
This work was supported in part by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant C, JP18K05460).
Abstract
The terpene core structure of suaveolindoles was synthesized through a concise route in a time-economical manner. A scalable synthetic route from pulegone delivered the desired α,β,γ,δ-unsaturated ester in a brief period. By way of Eschenmoser–Claisen rearrangement, carbon side-chain moiety at the crowded double-allylic position was introduced stereoselectively.
Key words
terpene - time-economy synthesis - natural product synthesis - Claisen rearrangement - DFT calculationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1707-6593.
- Supporting Information
Publication History
Received: 10 November 2021
Accepted after revision: 26 November 2021
Accepted Manuscript online:
26 November 2021
Article published online:
17 December 2021
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References and Notes
- 1a Yoo H.-D, Cremin PA, Zeng L, Garo E, Williams CT, Lee CM, Goering MG, O’Neil-Johnson M, Eldridge GR, Hu J.-F. J. Nat. Prod. 2005; 68: 122
- 1b Williams RB, Hu J.-F, Olson KM, Norman VL, Goering MG, O’Neil-Johnson M, Eldridge GR, Starks CM. J. Nat. Prod. 2010; 73: 1008
- 1c Marcos IS, Moro RF, Costales I, Basabe P, Díez D. Nat. Prod. Rep. 2013; 30: 1509
- 2 Jakupovic J, Banerjee S, Bohlmann F, King RM, Robinson H. Tetrahedron 1986; 42: 1305
- 3a Leboeuf M, Hamonnière M, Cavé A, Gottlieb HE, Kunesch N, Wenkert E. Tetrahedron Lett. 1976; 17: 3559
- 3b Kunesch N, Cavé A, Leboeuf M, Hocquemiller R, Dubois G, Guittet E, Lallemand J.-Y. Tetrahedron Lett. 1985; 26: 4937
- 4 Velthuisen EJ, Danishefsky SJ. J. Am. Chem. Soc. 2007; 129: 10640
- 5a Marcos IS, Moro RF, Costales I, Basabe P, Díez D, Mollinedo F, Urones JG. Tetrahedron 2012; 68: 7932
- 5b Marcos IS, Moro RF, Costales I, Basabe P, Díez D, Mollinedo F, Urones JG. Tetrahedron 2013; 69: 7285
- 5c Marcos IS, Moro RF, Costales I, Basabe P, Díez D, Gil A, Mollinedo F, Pérez-de la Rosa F, Pérez-Roth E, Padrón JM. Eur. J. Med. Chem. 2014; 73: 265
- 7 Corbu A, Aquino M, Perez M, Gandara Z, Arseniyadis S. Eur. J. Org. Chem. 2009; 6386
- 8a LeGay CM, Gorobets E, Iftinca M, Ramachandran R, Altier C, Derksen DJ. Org. Lett. 2016; 18: 2746
- 8b Gabriëls S, Van Haver D, Vandewalle M, De Clercq P, Viterbo D. Eur. J. Org. Chem. 1999; 1803
- 8c Camps F, Coll J, Guitart J. Tetrahedron 1986; 42: 4603
- 9 Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
- 11a Luche JL. J. Am. Chem. Soc. 1978; 100: 2226
- 11b Gemal AL, Luche JL. J. Am. Chem. Soc. 1981; 103: 5454
- 12 For successful example of conjugate addition to more reactive α,β,γ,δ-unsaturated diesters, see: Hatano M, Mizuno M, Ishihara K. Org. Lett. 2016; 18: 4462
- 13 The Claisen Rearrangement: Methods and Applications . Hiersemann M, Nubbemeyer U. Wiley-VCH; Weinheim: 2007
For review on the isolation and synthesis of the indolosesquiterpenes, see: